Sleepy Hollow Country Club

Frequently Asked Questions

How can I, a non-member, get a tee time at Sleepy Hollow Country Club?

Sleepy Hollow is a highly exclusive private club, so you'll need an invitation from a member to experience its Tillinghast magic. We recommend reaching out to your network or exploring charity events that occasionally offer rounds here; it's truly worth the effort to play.

What are the must-see holes or views at Sleepy Hollow, especially for a first-timer?

You absolutely cannot miss the iconic stretch from the 12th through the 16th, especially the par-3 16th with its dramatic Hudson River backdrop. The clubhouse itself, perched high above the course, offers breathtaking panoramic views that are perfect for a post-round drink.

When is the best time of year to play Sleepy Hollow for optimal conditions and scenery?

We always recommend late spring (May-June) or early fall (September-October) for the best experience. The course is in pristine condition, and the Hudson Valley foliage during autumn is simply spectacular, adding another layer of beauty to an already stunning layout.

What kind of challenge does Sleepy Hollow present, and how does the Tillinghast design influence play?

Tillinghast's genius shines through with strategic bunkering and greens that demand precision, not just power. You'll find yourself constantly thinking about angles and shot placement, making it a true test of golf strategy rather than just brute strength.

Beyond the golf, what's the overall atmosphere and experience like at Sleepy Hollow Country Club?

The club exudes a timeless elegance without being stuffy; it's steeped in history but feels welcoming. Expect impeccable service and a relaxed, sophisticated vibe, perfect for unwinding after your round and soaking in the rich heritage of the place.